Pisa and Florence Private Tour with Wine Tasting

Pisa and Florence Private Tour with Wine Tasting: A Day to Remember in Tuscany

If you’re looking to see Italy’s iconic cities with a touch of private luxury, this full-day tour from Livorno offers a wonderful blend of history, art, and authentic Tuscan flavors. For about $1,300 per group (up to 7 people), you get the chance to explore Pisa’s famous Leaning Tower, walk through Florence’s stunning piazzas, and top it off with a private wine tasting in the Chianti hills. It’s a curated experience that appeals to those who want a personalized, relaxed, yet comprehensive taste of Tuscany.

What we really love about this tour is the balanced itinerary—it hits all the major sights without feeling rushed, thanks to the private transport and expert guides. The scenic drive through Tuscan countryside offers a taste of Italy’s rolling hills and vineyards. Plus, the wine tasting at a well-regarded organic farm provides a genuine taste of local produce and craftsmanship.

A possible drawback could be the tight schedule—you’ll be on the move for about 9 hours, which may feel a bit rushed if you love lingering at each site. Also, while the tour covers many highlights, tickets to climb the Leaning Tower or enter Florence’s cathedral are not included, so you might want to budget extra if you’re eager to go inside these landmarks.

This experience suits travelers who enjoy a well-organized day of sightseeing combined with authentic local experiences. It’s particularly ideal for those who appreciate knowledgeable guides, beautiful views, and excellent wine.

This experience made our article of The 15 Best Wine Tours In Livorno.

Key Points

• Private, Comfortable Transportation ensures a stress-free day without worrying about navigating Italy’s busy streets.
• Expert Guides provide insightful commentary, making the history and architecture come alive.
• Flexible Itinerary allows you to enjoy Pisa’s Leaning Tower, Florence’s main sights, and a scenic wine tasting without rushing.
• Authentic Tuscan Experience with a private wine tour, tasting organic wines, and local cured meats.
• Beautiful Scenic Drives through the rolling hills of Chianti, offering perfect photo opportunities.
• Transparent Pricing with no hidden costs, but optional site tickets may need to be purchased separately.

The Complete Experience: A Deep Dive into the Tour

Convenient Private Transport and Starting Point

The tour begins with hotel or port pickup in Livorno, making logistics seamless and straightforward. Traveling in a luxury Mercedes van means you’ll ride comfortably, with air conditioning and onboard WiFi, perfect for relaxing or catching up on travel planning. The private driver-guide ensures your day stays flexible, allowing for adjustments based on your interests or pace.

Stop 1: Piazza dei Cavalieri – Pisa’s Renaissance Heart

Your first stop is Piazza dei Cavalieri, Pisa’s political and cultural hub during the Renaissance. This refined square is often overlooked by travelers heading straight to the Leaning Tower but is a delightful introduction to Pisa’s historical grandeur. You’ll see beautiful façades by Giorgio Vasari, including the Palazzo della Carovana and the Palazzo dell’Orologio.

A highlight is the statue of Cosimo I de Medici and the shell-shaped fountain, which symbolize Pisa’s naval strength. The Church of Santo Stefano dei Cavalieri adds to the charm with its decorated interiors and Ottoman banners.

Reviewers mention that most buildings aren’t open to the public, but simply strolling through the square offers a serene moment of history, architecture, and quiet. It’s an excellent short stop that sets the tone for the day.

Stop 2: The Leaning Tower of Pisa – World’s Most Famous Tilt

Next, you visit Piazza dei Miracoli, home to Pisa’s iconic Leaning Tower. While entry to the square is free, the tickets to climb the tower or enter the cathedral aren’t included, giving you flexibility on how to enjoy this UNESCO site.

You’ll have about 30 minutes to admire the architecture, take classic photos (like the one “holding up” the tower), and perhaps enjoy a coffee at a nearby café with a view. The cathedral and baptistery are also part of the complex, and if you wish to explore inside, you’ll need to book tickets separately.

Visitors often comment on how impressed they are by the architecture and how the tilt of the tower adds a whimsical charm. One reviewer noted, “We visited Pisa and Florence which are the most wonderful parts of Italy. Mike took us the beautiful hillside too,” highlighting how this tour balances major sights with scenic drives.

The Scenic Drive Through Tuscany

Between Pisa and Florence, the scenery shifts from urban to countryside, with gentle hills, vineyards, and olive groves. The drive itself is part of the experience, giving you a sense of the Tuscan landscape. Many travelers find this part to be calming and picturesque, a perfect prelude to Florence.

Stop 3: Piazzale Michelangelo – Florence’s Best Viewpoint

Arriving in Florence, the view from Piazzale Michelangelo is unforgettable. Standing on a hill just outside the city center, you’ll see a panoramic vista stretching from the red dome of the Duomo to the towers of Palazzo Vecchio and the Arno River.

A replica of Michelangelo’s David adds to the charm, and many reviewers say this is the best spot to see Florence from above. It’s an ideal place to pause, take photos, and enjoy a quick espresso in a local café while soaking in the beauty of the city.

Stop 4: Piazza del Duomo – Florence’s Architectural Gem

Walking into Florence’s Piazza del Duomo, you’re immediately struck by the magnificent façade of the cathedral, highlighted by Brunelleschi’s red-tiled dome. You’ll get a close-up look at Giotto’s Bell Tower and the Baptistery of San Giovanni, both stunning examples of Renaissance craftsmanship.

While the interior isn’t part of this tour, you’d likely be captivated by the frescoes and stained glass visible from outside. The square is lively and filled with street musicians and vendors, embodying Florence’s vibrant atmosphere.

Stop 5: Piazza della Signoria – The Heart of Florence

This square is absolutely packed with history and art. The Palazzo Vecchio dominates with its fortress-like look, and the Loggia dei Lanzi showcases notable sculptures, including Perseus with Medusa’s Head and The Rape of the Sabine Women.

A statue of Michelangelo’s David replica stands prominently, and the Neptune Fountain adds to the regal ambiance. Many visitors describe this as the ideal place to sit, soak up the atmosphere, and watch street performers.

Stop 6: Ponte Vecchio – Florence’s Most Famous Bridge

No visit to Florence is complete without a walk across Ponte Vecchio. This medieval bridge is unique with its rows of jewelry shops, originally butchers, now upscale goldsmiths. You’ll enjoy views of the Arno River, and if you look up, you’ll see the Vasari Corridor, a covered passageway built for the Medici family.

Many reviews highlight how the shops and views make this a special experience, and it’s a great spot for photos and browsing jewelry.

Stop 7: Wine Tasting in the Chianti Hills

A real highlight of this tour is the private wine tasting at Fattoria San Michele a Torri, just 15 km from Florence. Known for certified organic wines and award-winning olive oil, this farm offers a guided tour of their wine cellar and olive oil production.

You’ll sample three premium organic wines, including Chianti Classico and Chianti Colli Fiorentini, paired with homemade bread, Laudemio extra-virgin olive oil, and cured meats.

The reviews rave about the knowledgeable guides and authentic tasting experience, with one saying, “We loved the way Enzo explained the wine and olive oil making process,” emphasizing the personalized insight provided.

What the Tour Means for You

This tour offers a practical combination of cultural highlights and authentic Tuscan flavors. The private transport ensures comfort and flexibility, especially valuable in unpredictable weather or if you prefer a less crowded experience.

The guided visits to Pisa and Florence provide context and stories that make the architecture and art more meaningful. The scenic drives through the countryside and the private wine tasting are what set this apart from self-guided day trips.

However, keep in mind the duration—about 9 hours—so it’s best suited for travelers who want a full, immersive day rather than slow-paced sightseeing. Also, you’ll need to purchase separate tickets if you want inside access to certain landmarks like the Leaning Tower or Florence’s cathedral.

Who Should Consider This Tour?

This experience is ideal for couples, small groups, or families seeking a personalized, well-organized day with a mix of history, art, and wine. It’s perfect if you value guidance from knowledgeable locals and enjoy deluxe transport and authentic tastings. If you love scenic drives, beautiful views, and want to avoid the hassle of planning every detail, this tour ticks all the boxes.

FAQs

Is this tour suitable for everyone?
Most travelers can participate, as it’s designed for a small group with private transportation and guided visits. If you enjoy cultural sights and wine, you’ll be in your element.

Does the tour include tickets for climbing the Leaning Tower?
No, tickets for the tower or entrance to the cathedral are not included, so you may want to arrange those separately if you wish to go inside.

What is included in the price?
Round-trip private transport, hotel/port pickup and drop-off, a driver-guide, live commentary, luxury vehicle, onboard WiFi, and a private wine tasting.

Are meals included?
No, lunch is not included, so you’ll have time for a meal at your own expense, perhaps in Florence or at the winery.

How long is the drive between Pisa and Florence?
The scenic drive through Tuscany takes approximately 1 to 1.5 hours, offering wonderful views along the way.

Can I customize the itinerary?
Yes, you can request tickets to popular sites or a reservation at a local restaurant, provided you communicate your preferences in advance.

What if the weather is bad?
Since most stops are outdoors or involve walking outside, weather can affect the experience. Your guide can adapt the schedule accordingly.

Is the wine tasting included in the price?
Yes, the wine and olive oil tasting at Fattoria San Michele a Torri is part of the package, offering three organic wines and local delicacies.

Final Thoughts

This private Pisa and Florence tour paired with a wine tasting offers a well-rounded, comfortable way to capture the essence of Tuscany in a single day. It’s especially suited for those who appreciate cultural insights, scenic drives, and authentic local flavors. The personalized guidance and private transport make it a luxurious yet practical choice for travelers who want to maximize their time and enjoyment without the hassle of navigating alone.

While the cost might seem high, the value lies in the convenience, expert-guided visits, and exclusive wine experience—which are often hard to replicate on your own. If you’re after a memorable, smooth, and enriching day trip in Italy’s most classic regions, this tour could be just what you’re looking for.

In the end, this experience is perfect for those who want a comprehensive taste of Tuscany’s highlights in style, with a touch of wine and breathtaking landscapes thrown in. Whether you’re celebrating a special occasion or simply want to see Italy’s best sights comfortably, it’s a day worth considering.